Full-time
Senior, lead, principal or architect roles.
- Technical direction and architecture
- Hands-on delivery alongside the team
- Leading, mentoring and advising stakeholders
- Hamilton-based: NZ remote or hybrid, or international remote
Open to roles, contracts & projects
Hamilton, NZ · Remote worldwide
Henry Penny
Senior Software ArchitectAI Agentic Workflow LeadTechnical Leader
I build software, lead the teams that ship it, and wire AI into how they work.
25+ years building and leading software delivery. Now I apply AI agentic workflows to real engineering: designing agent roles, orchestrating deterministic AI pipelines, and bringing structured automation to the whole development lifecycle.
work flowing through an agentic pipeline
Work with me
Four ways to work together.
Pick the one that fits. Each goes straight to a conversation, not a sales funnel.
Contract
Short or long-term engagements, embedded with your team.
- Taking ownership of complex or inherited systems
- Stabilising, remediating and migrating
- Working with agency and in-house teams
- Clear handover when the engagement ends
Project build
Web apps, platforms and AWS infrastructure, built properly.
- Scoping and architecture
- Build, test and deploy
- Serverless and container workloads on AWS
- Rescuing legacy or undocumented systems
AI workflow consulting
Adopt agentic AI in a way your engineering practice can rely on.
- Agent role and responsibility design
- Deterministic orchestration patterns
- AI in CI/CD: triage, PRs, bug fixes
- AI-generated BDD, end-to-end and unit tests
AI & agentic workflows
Agents with job descriptions, not a chatbot in a tab.
Most teams bolt an assistant onto the editor and stop there. I design the workflow first: which agent does what, what it is allowed to touch, and how its output is checked. Then I make it repeatable.
Methodology
Designed AI agentic workflow methodologies for a software agency: agent roles, responsibilities, skills and orchestration patterns.
Orchestration
Prototyping a Rust CLI that executes deterministic workflows and shells out to GitHub Copilot CLI for each step.
CI/CD integration
Integrating agentic orchestration into GitHub CI/CD: automated issue triage, PR generation and AI-assisted bug fixes.
Quality automation
AI-generated Cucumber BDD, end-to-end and unit tests as part of a wider quality automation strategy.
Leadership
Primary thought leader in the agency's AI re-tooling initiative.
agentic-workflow · simulated
$ orchestrate run fix-bug --issue 142 workflow fix-bug · 5 steps · deterministic [triage] classify issue → bug · area: billing ✓ labelled and assigned [plan] read code, propose change ✓ plan: 2 files, 1 migration [test] generate failing Cucumber scenario ✓ scenario fails as expected [build] apply fix via copilot ✓ unit + e2e + bdd passing [review] open PR for human review ✓ PR opened · awaiting approval done · a human merges, not the agent
Selected work
Hard systems, made dependable.
Four engagements, told plainly: what was wrong, what I did, where it ended up.
Putti · global Web3 client
Rescuing an undocumented serverless Web3 platform
- Problem
- A blockchain rewards platform for a global Web3 client. Fully serverless, undocumented, and inherited with no handover.
- What I did
- Took ownership of the platform and learned it from the code up
- Stabilised and evolved it on AWS Lambda, SQS, DynamoDB, EventBridge and API Gateway, managed in Terraform
- Led a mixed agency and client team
- Advised C-level and VP stakeholders
- Outcome
- A stable platform the client could keep building on, with a team and a direction.
- Serverless
- Terraform
- Web3
- Leadership
HealthSafe
Stabilising and migrating government-facing legacy platforms
- Problem
- Two legacy platforms, SecurePass and a Risk Management System, serving clients including central government. Both needed security remediation and a better home.
- What I did
- Embedded as architect across both platforms
- Led security remediation
- Migrated both platforms to AWS ECS
- Tuned databases and optimised infrastructure
- Outcome
- Both platforms running on ECS, with reduced hosting costs.
- AWS ECS
- Security
- Legacy
- Cost
Frello (formerly Friendly Manager)
Unified SSO for a platform merger
- Problem
- Hello Club and Friendly Manager were merging into one sports club management platform. Users needed one identity across both.
- What I did
- Set technical direction for the merger
- Built an SSO solution on AWS Cognito, TypeScript Lambdas and DynamoDB
- Implemented OAuth and OIDC with PKCE
- Provisioned AWS Well-Architected infrastructure via Control Tower, with AWS architects
- Outcome
- A standards-based SSO for the merged platform, on a well-architected AWS foundation.
- Cognito
- OIDC
- PKCE
- Control Tower
Putti
Agentic AI re-tooling of an engineering agency
- Problem
- An agency wanting AI to change how it delivers software, in a structured way rather than ad hoc.
- What I did
- Designed the agentic workflow methodology: roles, responsibilities, skills, orchestration
- Prototyping a Rust CLI for deterministic workflows over GitHub Copilot CLI
- Integrating orchestration into GitHub CI/CD for triage, PRs and bug fixes
- Introduced AI-generated Cucumber BDD, end-to-end and unit tests
- Outcome
- An agency-wide AI re-tooling initiative, with me as its primary thought leader.
- Agentic AI
- Rust
- GitHub Actions
- BDD
Experience
25+ years of shipping.
From team lead to technical director to architect, always close to the code.
Nov 2023 – present
Lead Developer · Putti
- Blockchain rewards platform for a global Web3 client: took ownership of an undocumented serverless platform with no handover, then stabilised and evolved it
- Fully serverless AWS: Lambda, SQS, DynamoDB, EventBridge, API Gateway, Terraform
- Led a mixed agency/client team and advised C-level and VP stakeholders
- HealthSafe (2024 – present): embedded architect on SecurePass and a Risk Management System serving clients including central government. Security remediation, migration of both to AWS ECS, and reduced hosting costs through database tuning and infrastructure optimisation
- Leading Putti's agency-wide AI re-tooling initiative
Jul 2021 – Nov 2023
Senior Software Architect · Frello (formerly Friendly Manager)
- Technical direction for the merger of Hello Club and Friendly Manager into one sports club management platform
- Built an SSO solution on AWS Cognito, TypeScript Lambdas and DynamoDB (OAuth / OIDC with PKCE)
- Provisioned AWS Well-Architected infrastructure via Control Tower with AWS architects
2018 – 2021
Freelance Consultant · Independent
- Speedster: Apply Online built with Vue.js and Craft Commerce, integrated with the Electricity Authority EMI API, NZ Post and others
- NZ Dental Association: "Checkup", a self-auditing platform built on Symfony
- Partsworld: backend rebuild and dismantler inventory integration, reporting to the Board
2017 – 2018
Contract Developer · Figured / Agrigate
- Laravel and Vue.js
- John Deere API integration
2012 – 2017
Technical Director · Supply Ltd
- Ran all web development: led and mentored the team, pitching and delivery
- Led the BurgerFuel website rebuild
2006 – 2012
Development Director / Application Architect · Fresh Media Group / Ceros
- Oversaw development across five companies
- Built the Ceros media player from scratch
- Led integration with Sears' online shopping cart
- Advised the board
Earlier
Earlier roles
- The Grand Union · London
- Banner · London
- NetConcepts
- Datacom / Air New Zealand · Team lead of 7, Tivoli Access Manager implementation
- Intaz · Java team lead of 7 on SafeTSmart; Technical BA in Melbourne
Qualifications
- BSc Computer Science & Physics
- NZ Certificate of Engineering (Electronics and Computing)
- Postgraduate papers, University of Waikato: Machine Learning Algorithms (COMP521), Metaheuristic Algorithms (COMPX556)
Skills
The toolkit.
Grouped by what they are for. Pick a cluster to focus it.
AI & Agents
Designing and running agentic workflows
- GitHub Copilot CLI
- Agentic orchestration
- Deterministic workflow design
- LLM-assisted testing
- CI/CD AI integration
- Rust CLI tooling
AWS & IaC
Serverless, containers and infrastructure as code
- Lambda
- ECS
- DynamoDB
- S3
- SQS
- EventBridge
- API Gateway
- Cognito
- Aurora
- Control Tower
- CloudFormation
- CDK
- Terraform
- SST
- Serverless Framework
Backend
Services, APIs and data
- TypeScript
- Node.js
- NestJS
- Express
- PHP 5–8
- Symfony
- Laravel
- MySQL
- PostgreSQL
- MongoDB
Frontend
Interfaces people use
- React
- Vue.js
- Vite
- Pinia
- HTML/CSS/SASS
Auth & APIs
Identity and integration
- OAuth
- OIDC
- PKCE
- REST
DevOps
Build, test, ship
- GitHub Actions
- GitLab
- Docker
- CI/CD
Web3
Chains in production
- Ethereum
- ROOT network
Henry is one of the most pragmatic development level tech heads I've ever met or worked with.